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Chicago, IL: Point of Interest Map
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Chicago, IL Vacation Packages


Chicago, on Lake Michigan in Illinois, is the third-largest city in the United States and the largest city in the Midwest region. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. A must-visit place for tourists is ritzy Michigan Avenue, part of which is the famed `Magnificent Mile`. Chicago is renowned for its museums, including the Art Institute of Chicago, which sits between Grant Park and the beginning of historic Route 66.

Best Chicago, IL Vacation Packages:

Chicago

Chicago, IL

Hotels and Activities

SUGGESTED Chicago, IL VACATION PACKAGES:

  • Chicago and Naperville (Self Drive)
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  • Enjoy this Self-Drive Package to venture through the "Land of Lincoln'; Illinois, discovering these two charming cities. With a Rental Car, combine and visit; Chicago (renowned for its bold architecture, like the "Sears Tower", museums and festivals). After that, have a wonderful stay in Naperville; with an "expected beach surprise": The Naperville's Centennial Beach (historic double quarry alongside the DuPage River, with a white sand beach). The site also offer an important Outdoor History Museum, with a collection of historical buildings and structures from the historic Naperville settlement. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into and out of Chicago
    • Rental Car for 3 days
    • Pick Up/Drop Off: Chicago Airport
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Naperville
    • Driving Time
      Chicago - Naperville: 55 mins. approx.
      Naperville - Chicago Airport: 45 mins. approx.



  • Chicago and Rockford (Self Drive)
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  • Cosmopolitan city, open green spaces and music await you with this Self-Drive Package in these two cities in Illinois State. Start this trip with a visit to "The Windy City"; Chicago (famed for its bold architecture, with the Sears Tower; with its museums and many loyal sports fans). After that, drive to Rockford ("The Forest City"; with some of the most beautiful Japanese Gardens in the USA. Also its home of the American Rock Band "Chip Trick"). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into and out of Chicago
    • Rental Car for 3 days
    • Pick Up/Drop Off: Chicago Airport
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Rockford
    • Driving Time
      Chicago - Rockford: 1 hr. 30 mins. approx.
      Rockford - Chicago Airport: 1 hrs. 15 mins. approx.



  • Chicago and St. Louis (Self Drive)
    6 nights from $916*
  • Take Illinois and Missouri into your own hands, travelling between this popular cities with a rental car. Visit Chicago (Famed for its bold architecture and renowned for its museums and many loyal sports fans) and St Louis (a major city in Missouri along the Mississippi River, known for the Gateway Arch, the tallest monument constructed in the United States). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of St Louis Airport
    • Rental Car for 7 days
    • Hotel for 3 nights in Chicago
    • Hotel for 3 nights in St Louis
    • Driving Time
      Chicago - St Louis: 4hr 35mn approx.



  • Chicago and the Lake Michigan Shore (Self Drive)
    7 nights from $2,221*
  • This self-drive, independent vacation package will introduce you to Illinois and Wisconsin. Visit Chicago, on Lake Michigan in also called `The wind city ‘and it will blow you away with its steely skyscrapers, museums and rocking festivals, then, drive to Illinois State Beach and Lake Michigan Shore South (sprawling waterfront of activity and beauty, Traveling the towns throughout the Shore you will find shopping destinations, to world-class golf courses, to family-friendly attractions and casinos). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Milwaukee
    • Rental Car for 8 days
    • Hotel for 3 nights in Chicago, IL
    • Hotel for 2 nights in Illinois State Beach, IL
    • Hotel for 2 nights in Lake Michigan Shore South, WI
    • Driving Time
      Chicago, IL - Illinois State Beach, IL: 1 hrs 3 mins approx.
      Illinois State Beach, IL- Lake Michigan Shore South, WI: 3 hr. 8 mins. approx.



  • Chicago and the Quad Cities (Self Drive)
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  • This self-drive, independent vacation package will introduce you to these beautiful cities through Illinois. Combine Chicago (The wind city will blow you away with its steely skyscrapers, museums and rocking festivals) and Quad Cities (a region of five cities in the U.S. states of Iowa and Illinois: Davenport and Bettendorf in southeastern Iowa, and Rock Island, Moline, and East Moline in northwestern Illinois); with a Rental Car. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Quad Cities
    • Rental Car for 6 days
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Quad Cities
    • Driving Time
      Chicago - Quad Cities: 2 hrs. 51 mins. approx.



  • Chicago Getaway
    4 nights from $292*
  • This self-drive, independent vacation package will introduce you Illinois. Visit Chicago, on Lake Michigan in also called `The wind city ‘and it will blow you away with its steely skyscrapers, museums and rocking festivals. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight in and out of Chicago
    • Rental Car for 5 days
    • Hotel for 4 nights in Aspen


  • Maldives Escape
    5 nights from $1,163*
  • Get away from it all with this customizable package that lets you visit Maldives Island, for a trip that won't be forgotten. Explore Maldives Island, a small island nation in South Asia, situated in the Arabian Sea of the Indian Ocean, known for their natural environment including the blue ocean, white beaches, and clean air. This is a flexible vacation package. Select your number of nights in each city, desired hotel, and activities.
    Included:
    • Flight in and out of Maldives island
    • Hotel for 5 nights in Maldives
    • Please note that transfer in Maldives are not included. Please contact us for arrangements.


  • Route 66 - Illinois to Oklahoma the Highlights (Self Drive)
    7 nights from $909*
  • Venture from east to west along the iconic Route 66, the most famous U.S. Highway System. Popular sights for families, adventurers, and lovers of small town Americana, beckon visitors to explore the heart of the country. Start in Illinois, with a stay in "The Windy City" - Chicago (famed for its bold architecture and renowned for its museums and many loyal sports fans), then journey to Missouri known as the "Show Me State" while exploring St. Louis (known for the Gateway Arch, the tallest monument constructed in the U.S.) and Springfield (the "Queen City of the Ozarks" which offers beautiful and scenic outdoor recreational activities). Before ending this whirlwind trip, your next stop is in Oklahoma, with a pleasant stay in its capital city; Oklahoma City (known for its cowboy culture and capital complex, surrounded by working oil wells). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago and out of Oklahoma City
    • Rental Car for 8 days
    • Hotel for 3 nights in Chicago
    • Hotel for 1 night in St. Louis
    • Hotel for 1 night in Springfield
    • Hotel for 2 nights in Oklahoma City
    • Driving Time
      Chicago - St. Louis: 5 hrs 25 mins approx.
      St. Louis - Springfield: 3 hrs 20 mins approx.
      Springfield - Oklahoma City: 4 hrs 15 mins approx.



  • Route 66 - Illinois to Texas the Long Ride (Self Drive)
    15 nights from $1,754*
  • Explore iconic Route 66 on a long ride from east to west, venturing through Illinois, Missouri, Oklahoma, and Texas - with nearly endless opportunities to experience culture, excitement, and beauty. Combine Chicago (set on beautiful Lake Michigan the city is well regarded for interesting architecture - like the Sears Tower - and its cultural highlights from museums to theaters and more), Springfield, Illinois (home of President Abraham Lincoln as well as his Presidential Library), St. Louis (whose beautiful and famous Gateway Arch welcomes visitors to this city on the Mississippi River), Springfield, Missouri (an Ozark city with lots of Route 66 history), Tulsa (Oklahoma`s vibrant second-largest city, with a sizable arts scene), Oklahoma City (the capital of Oklahoma and home to the National Cowboy and Western Heritage Museum and the Oklahoma City Memorial) and finally Amarillo (nicknamed `The Yellow Rose of Texas`, boasts a great food scene, historic districts, and easy access to Palo Duro Canyon). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Chicago Airport and out of Oklahoma City Airport
    • Rental Car for 16 days
    • Hotel for 3 nights in Chicago
    • Hotel for 2 nights in Springfield, IL
    • Hotel for 2 nights in St. Louis
    • Hotel for 2 nights in Springfield, MO
    • Hotel for 2 nights in Tulsa
    • Hotel for 2 nights in Oklahoma City
    • Hotel for 2 nights in Amarillo
    • Driving Time
      Chicago– Springfield, IL: 3hrs 14min approx.
      Springfield, IL- St. Louis: 1 hr 28 mins approx.
      St. Louis- Springfield, MO: 3hrs 22mins approx.
      Springfield, MO- Tulsa: 3 hrs approx.
      Tulsa - Oklahoma City: 1hrs 34mins approx.
      Oklahoma City - Amarillo: 4hrs approx.



  • St. Louis and Chicago (Self Drive)
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  • Venture through these beautiful cities of Illinois and Missouri, exploring its natural landscapes and nightlife with a rental car. Combine St Louis (Offers a 630 ft Gateway Arch that pays homage to Thomas Jefferson and St. Louis`s position as the getaway to the West) and Chicago (The wind city will blow you away with its steely skycrapers, museums and rocking festivals). This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into St Louis and out of Chicago Airport
    • Rental Car for 7 days
    • Hotel for 3 nights in St Louis
    • Hotel for 3 nights in Chicago
    • Driving Time
      St Louis - Chicago: 4 hrs. 35mn approx.



  • Bahrain and Maldives by Air
    6 nights from $2,020*
  • Bahrain and Maldives are waiting to be explored, offering historical charm and exciting attractions with flights between cities!. Start in Bahrain, visiting Manama (capital and largest city of the state and emirate of Bahrain, now is a modern capital with an economy based around the sales promotion industry and famous for its air-conditioned ancient bazaars (souks) along the historic centre). Finally, enjoy Maldives Island (a small island nation in South Asia, situated in the Arabian Sea of the Indian Ocean). This is a flexible package. Select your number of nights in each city, desired hotel and activities.
    Included:
    • Flight into Manama and out of Male
    • Hotel for 3 nights in Manama
    • Flight from Manama to Male (Maldives)
    • Hotel for 3 nights in Maldives
    • Please note that transfer in Maldives are not included. Please contact us for arrangements.


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